this is harder and harder to do these days with high tech surveillance. Pretty much every major railyard has infrared cameras to detect hoppers. Plus cameras up the wasu.
I have known some dudes who did it back in the day and they had all sorts of tips and tricks. Wish I could remember. There was also some train hopping guide If I recall correctly. It was passed around in vagrant circles. Might be able to track it down and torrent it or something.
I know there is a risk of death when you are getting on and off. Plus the bulls (security) at train yards are known for beating the shit out of hoppers.
Probably meet a good deal of sketch people. But also some real genuine characters as well. But this isn't Jack Kerouac's 1950s, shit its not even 2008 (that's when those dudes I knew where doing it). I'd be surprised if it's really all that common a practice anymore.
Maybe look into the NUMTOT community (New Urbanist Memes for Transit-Oriented Teens). A bunch a online nerds who fetishize urban public transit.
I think the biggest things would be knowing the train schedules. These are often leaked and you can find them on the deep web. Then knowing where to hop on and get off where you wont be seen or caught. Plus when the train is going at the right speed so you don't fall and get crushed. Also you gotta know which cars you can hop and ride in and which you can't.
That's about all I know about it. Hoping trains in theory sounds like an incredible adventure with scenic views through hidden corners of the world. Not sure how much that fantasy holds up in reality, as I have never done it myself. But there are a lot of risks involved. Especially in the hyper surveillance era.
Let me know what you find though, cause if that shit is super easy I might be game to join you. But for real I probably wouldn't, nor would I advise it cause it's crazy dangerous.